Sodium Methoxide → (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanol

HRID 1677066Notes

Reaction equation

HRID 1677066 reaction equation
C[O-].[Na+].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[NH:16][C@@H:15]([C@@H:17]([O:19]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH3:18])[CH2:14][O:13][CH2:12]2)=[CH:7][CH:6]=1>CO>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C@H:11]2[NH:16][C@@H:15]([C@@H:17]([OH:19])[CH3:18])[CH2:14][O:13][CH2:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 673717534-nitrobenzoic acid (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholin-3-yl]ethyl ester

Product 1

HCID 68716014(S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholine-3-yl]ethanolYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (1.9 mL, 28% methanol solution) was added to a methanol (40 mL) solution of 4-nitrobenzoic acid (S)-1-[(3R,5R)-5-(4-chlorophenyl)morpholin-3 yl]ethyl ester (1.46 g). Stirring was continued for 1 hour at room temperature. The solvent was removed under a vacuum, and ethyl acetate and water were added, and the organic layer was partitioned. The organic layer was washed with brine, and the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/3), and the title compound (833 mg) was obtained. The physical property values are as follows.

Workup

  1. customThe solvent was removed under a vacuum, and ethyl acetate and water
  2. additionwere added
  3. customthe organic layer was partitioned
  4. washThe organic layer was washed with brine
  5. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed under a vacuum
  7. customthe residue was purified by silica gel column chromatography (heptane/ethyl acetate 9/1→1/3)

Sources & evidence

ORD record
ord-6224207b89754f37b27a0d81ee674d15
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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